MOST EFFICIENT INTRAMOLECULAR GENERAL ACID CATALYSIS OF ACETAL HYDROLYSIS BY THE CARBOXY GROUP

被引:35
作者
KIRBY, AJ
PARKINSON, A
机构
关键词
D O I
10.1039/c39940000707
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The hydrolysis of 4-methoxymethoxybenzisoxazole-3-carboxylic acid (halflife 31 s at 39-degrees-C) is the fastest measured for a methoxymethyl acetal: catalysis by the neighbouring CO2H group is facilitated by a strong intramolecular hydrogen bond.
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页码:707 / 708
页数:2
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共 13 条
[1]  
BUFFET C, 1976, RECL TRAV CHIM PAY B, V95, P1
[2]  
CAPON B, 1963, TETRAHEDRON LETT, P911
[3]   ROLE OF CARBOXY-GROUP IN INTRAMOLECULAR CATALYSIS OF ACETAL HYDROLYSIS - HYDROLYSIS OF SUBSTITUTED 2-METHOXYMETHOXYBENZOIC ACIDS [J].
CRAZE, GA ;
KIRBY, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (01) :61-66
[4]   DECARBOXYLATION OF BENZISOXAZOLE-3-CARBOXYLIC ACIDS - CATALYSIS BY EXTRACTION OF POSSIBLE RELEVANCE TO PROBLEM OF ENZYMATIC MECHANISM [J].
KEMP, DS ;
PAUL, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) :2553-+
[5]   PHYSICAL ORGANIC-CHEMISTRY OF BENZISOXAZOLES .3. MECHANISM AND EFFECTS OF SOLVENTS ON RATES OF DECARBOXYLATION OF BENZISOXAZOLE-3-CARBOXYLIC ACIDS [J].
KEMP, DS ;
PAUL, KG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (25) :7305-7312
[6]  
KEMP DS, 1975, J AM CHEM SOC, V97, P7313
[7]  
Kirby A.J., 1980, ADV PHYS ORG CHEM, V17, P183
[8]   MECHANISM AND STEREOELECTRONIC EFFECTS IN THE LYSOZYME REACTION [J].
KIRBY, AJ .
CRC CRITICAL REVIEWS IN BIOCHEMISTRY, 1987, 22 (04) :283-315
[9]   INTRAMOLECULAR PROTON-TRANSFER CATALYSIS OF NUCLEOPHILIC CATALYSIS OF ACETAL HYDROLYSIS - THE HYDROLYSIS OF 8-DIMETHYLAMINO-1-METHOXYMETHOXYNAPHTHALENE [J].
KIRBY, AJ ;
PERCY, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (07) :907-912
[10]   INTRAMOLECULAR NUCLEOPHILIC CATALYSIS OF GLUCOSIDE HYDROLYSIS BY THE 2-PHOSPHATE GROUP [J].
KIRBY, AJ ;
STROMBERG, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) :709-710